In building location-based services, it is important to present information in ways that fit with how individuals view and navigate the city. We conducted an adaptation of the 1970s Mental Maps study by Stanley Milgram in order to better understand differences in people’s views of the city based on their backgrounds and technology use. We correlated data from a demographic questionnaire with the map data from our participants to perform a first-of-its-kind statistical analysis on differences in hand-drawn city maps. We describe our study, findings, and design implications for location-based services.